UA73122C2 - Derivatives of benzodioxane, benzofuran or benzopyran substituted by aminoalkyl - Google Patents

Derivatives of benzodioxane, benzofuran or benzopyran substituted by aminoalkyl Download PDF

Info

Publication number: UA73122C2
Authority: UA; Ukraine
Prior art keywords: formula; group; alkyl; hydrogen; compound
Prior art date: 1999-06-02

Application number

UA2001128825A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Janssen Pharmaceutica Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-06-02

Filing date

2000-05-23

Publication date

2005-06-15

2000-05-23 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2005-06-15 Publication of UA73122C2 publication Critical patent/UA73122C2/uk

Links

IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title description 4
KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical group C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 title description 2
125000004103 aminoalkyl group Chemical group 0.000 title 1
BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical group C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 123
239000001257 hydrogen Substances 0.000 claims abstract description 44
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
150000003839 salts Chemical class 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 26
239000002253 acid Substances 0.000 claims abstract description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 15
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
239000001301 oxygen Substances 0.000 claims abstract description 14
229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 12
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
239000003814 drug Substances 0.000 claims abstract description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
239000011593 sulfur Chemical group 0.000 claims abstract description 6
229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 5
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
-1 homopiperidinyl Chemical group 0.000 claims description 30
150000002431 hydrogen Chemical class 0.000 claims description 23
239000002904 solvent Substances 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
239000002585 base Substances 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 11
125000003277 amino group Chemical group 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
239000003513 alkali Substances 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 4
230000007935 neutral effect Effects 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000001453 quaternary ammonium group Chemical class 0.000 claims description 3
230000009466 transformation Effects 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
125000004951 trihalomethoxy group Chemical group 0.000 claims description 2
125000004953 trihalomethyl group Chemical group 0.000 claims description 2
239000012458 free base Substances 0.000 claims 3
238000012876 topography Methods 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 45
238000009472 formulation Methods 0.000 abstract description 8
230000001771 impaired effect Effects 0.000 abstract description 7
101100490437 Mus musculus Acvrl1 gene Proteins 0.000 abstract 1
125000000815 N-oxide group Chemical group 0.000 abstract 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
210000002784 stomach Anatomy 0.000 description 31
239000000543 intermediate Substances 0.000 description 23
150000003254 radicals Chemical class 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
239000000243 solution Substances 0.000 description 17
230000002496 gastric effect Effects 0.000 description 15
239000003054 catalyst Substances 0.000 description 13
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
210000002599 gastric fundus Anatomy 0.000 description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000002347 injection Methods 0.000 description 8
239000007924 injection Substances 0.000 description 8
208000024891 symptom Diseases 0.000 description 8
238000012360 testing method Methods 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 7
239000000654 additive Substances 0.000 description 7
239000003480 eluent Substances 0.000 description 7
235000019441 ethanol Nutrition 0.000 description 7
239000003826 tablet Substances 0.000 description 7
BSRHATGBRQMDRF-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-2-ylmethanamine Chemical compound C1=CC=C2OC(CN)CCC2=C1 BSRHATGBRQMDRF-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
235000013305 food Nutrition 0.000 description 6
235000003599 food sweetener Nutrition 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000003765 sweetening agent Substances 0.000 description 6
239000005526 vasoconstrictor agent Substances 0.000 description 6
241000282472 Canis lupus familiaris Species 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
201000006549 dyspepsia Diseases 0.000 description 5
239000007788 liquid Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
229910052697 platinum Inorganic materials 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000000725 suspension Substances 0.000 description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
230000037406 food intake Effects 0.000 description 4
229960004592 isopropanol Drugs 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
239000007858 starting material Substances 0.000 description 4
229930192474 thiophene Natural products 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical compound [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000003044 adaptive effect Effects 0.000 description 3
230000000996 additive effect Effects 0.000 description 3
210000001841 basilar artery Anatomy 0.000 description 3
230000009286 beneficial effect Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
230000008602 contraction Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
235000012631 food intake Nutrition 0.000 description 3
239000008103 glucose Substances 0.000 description 3
235000011167 hydrochloric acid Nutrition 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
GVONPBONFIJAHJ-UHFFFAOYSA-N imidazolidin-4-one Chemical compound O=C1CNCN1 GVONPBONFIJAHJ-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
238000005932 reductive alkylation reaction Methods 0.000 description 3
230000004044 response Effects 0.000 description 3
230000002441 reversible effect Effects 0.000 description 3
230000036186 satiety Effects 0.000 description 3
235000019627 satiety Nutrition 0.000 description 3
229940076279 serotonin Drugs 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000375 suspending agent Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
206010019233 Headaches Diseases 0.000 description 2
206010021518 Impaired gastric emptying Diseases 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 2
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WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
NNOYLBKZPCUCQT-UHFFFAOYSA-L calcium;1,1-dioxo-1,2-benzothiazol-3-olate;heptahydrate Chemical compound O.O.O.O.O.O.O.[Ca+2].C1=CC=C2C([O-])=NS(=O)(=O)C2=C1.C1=CC=C2C([O-])=NS(=O)(=O)C2=C1 NNOYLBKZPCUCQT-UHFFFAOYSA-L 0.000 description 2
235000013736 caramel Nutrition 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000000969 carrier Substances 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
230000002490 cerebral effect Effects 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
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229940125904 compound 1 Drugs 0.000 description 2
229940125758 compound 15 Drugs 0.000 description 2
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UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000005259 measurement Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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239000003755 preservative agent Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
JADFCQKRKICRKI-UHFFFAOYSA-N quinoline;sulfane Chemical compound S.N1=CC=CC2=CC=CC=C21 JADFCQKRKICRKI-UHFFFAOYSA-N 0.000 description 2
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238000006722 reduction reaction Methods 0.000 description 2
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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NUFKRGBSZPCGQB-FLBSXDLDSA-N (3s)-3-amino-4-oxo-4-[[(2r)-1-oxo-1-[(2,2,4,4-tetramethylthietan-3-yl)amino]propan-2-yl]amino]butanoic acid;pentahydrate Chemical compound O.O.O.O.O.OC(=O)C[C@H](N)C(=O)N[C@H](C)C(=O)NC1C(C)(C)SC1(C)C.OC(=O)C[C@H](N)C(=O)N[C@H](C)C(=O)NC1C(C)(C)SC1(C)C NUFKRGBSZPCGQB-FLBSXDLDSA-N 0.000 description 1
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IAJINJSFYTZPEJ-UHFFFAOYSA-N 1h-pyrimidin-3-ium-2-one;chloride Chemical compound Cl.O=C1N=CC=CN1 IAJINJSFYTZPEJ-UHFFFAOYSA-N 0.000 description 1
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
PUMRUSBKNSBTAL-UHFFFAOYSA-N 3,4-dihydro-2h-chromene-2-carbaldehyde Chemical compound C1=CC=C2OC(C=O)CCC2=C1 PUMRUSBKNSBTAL-UHFFFAOYSA-N 0.000 description 1
GLXZQISZDFGOTI-UHFFFAOYSA-N 4-(2,3-dihydro-1,4-benzodioxin-3-yl)-3-(2-hydroxyethyl)-1-piperidin-1-ylimidazolidin-2-one Chemical class O1C(COC2=C1C=CC=C2)C2N(C(N(C2)N2CCCCC2)=O)CCO GLXZQISZDFGOTI-UHFFFAOYSA-N 0.000 description 1
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239000004334 sorbic acid Substances 0.000 description 1
SETMGIIITGNLAS-UHFFFAOYSA-N spizofurone Chemical compound O=C1C2=CC(C(=O)C)=CC=C2OC21CC2 SETMGIIITGNLAS-UHFFFAOYSA-N 0.000 description 1
229950001870 spizofurone Drugs 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
229940013618 stevioside Drugs 0.000 description 1
OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 description 1
235000019202 steviosides Nutrition 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
235000019408 sucralose Nutrition 0.000 description 1
BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
230000036269 ulceration Effects 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
230000003639 vasoconstrictive effect Effects 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000000811 xylitol Substances 0.000 description 1
235000010447 xylitol Nutrition 0.000 description 1
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
229960002675 xylitol Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Child & Adolescent Psychology (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Nutrition Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pyrane Compounds (AREA)

UA2001128825A 1999-06-02 2000-05-23 Derivatives of benzodioxane, benzofuran or benzopyran substituted by aminoalkyl UA73122C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP99201747		1999-06-02
PCT/EP2000/004746 WO2000075136A1 (en)	1999-06-02	2000-05-23	Aminoalkyl substituted (benzodioxan, benzofuran or benzopyran) derivatives

Publications (1)

Publication Number	Publication Date
UA73122C2 true UA73122C2 (en)	2005-06-15

Family

ID=8240260

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2001128825A UA73122C2 (en)	1999-06-02	2000-05-23	Derivatives of benzodioxane, benzofuran or benzopyran substituted by aminoalkyl

Country Status (33)

Country	Link
US (2)	US6864273B1 (pt)
EP (1)	EP1187829B1 (pt)
JP (1)	JP2003501427A (pt)
KR (1)	KR100699512B1 (pt)
CN (1)	CN1150191C (pt)
AR (1)	AR033334A1 (pt)
AT (1)	ATE256125T1 (pt)
AU (1)	AU773773B2 (pt)
BG (1)	BG65269B1 (pt)
BR (1)	BR0011237A (pt)
CA (1)	CA2374902C (pt)
CZ (1)	CZ20014177A3 (pt)
DE (1)	DE60007124T2 (pt)
DK (1)	DK1187829T3 (pt)
EA (1)	EA004645B1 (pt)
EE (1)	EE04780B1 (pt)
ES (1)	ES2212774T3 (pt)
HR (1)	HRP20010868A2 (pt)
HU (1)	HUP0201404A3 (pt)
IL (2)	IL146840A0 (pt)
MX (1)	MXPA01012330A (pt)
MY (1)	MY120618A (pt)
NO (1)	NO319953B1 (pt)
NZ (1)	NZ514993A (pt)
PL (1)	PL198552B1 (pt)
PT (1)	PT1187829E (pt)
SI (1)	SI1187829T1 (pt)
SK (1)	SK285619B6 (pt)
TR (1)	TR200103430T2 (pt)
TW (1)	TWI289559B (pt)
UA (1)	UA73122C2 (pt)
WO (1)	WO2000075136A1 (pt)
ZA (1)	ZA200109860B (pt)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
UA73123C2 (en)	1999-06-02	2005-06-15	Janssen Pharmaceutica Nv	Derivatives of benzodioxane, benzofuran or benzopyran substituted by pyrolidinyl, piperidinyl or homopiperidinyl
JO2352B1 (en) *	2000-06-22	2006-12-12	جانسين فارماسيوتيكا ان. في	Compounds for the treatment of non-adaptation of the bottom of the uterus
JO2654B1 (en)	2000-09-04	2012-06-17	شركة جانسين فارماسوتيكا ان. في	Multiple aryl caroxa amides are useful as lipid - lowering agents
JO2409B1 (en)	2000-11-21	2007-06-17	شركة جانسين فارماسوتيكا ان. في	Second-phenyl carboxy amides are useful as lipid-lowering agents
US20050176788A1 (en) *	2002-04-08	2005-08-11	Zeria Pharmaceutical Co., Ltd.	Therapeutic agent for food competence disorder in stomach
AU2006214233A1 (en)	2005-02-17	2006-08-24	Wyeth	Cycloalkylfused indole, benzothiophene, benzofuran and indene derivatives
SG11201401531RA (en)	2011-11-11	2014-07-30	Pfizer	2-thiopyrimidinones
BR112017022340A2 (pt)	2015-05-05	2018-07-10	Pfizer	2-tiopirimidinonas

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3910930A (en)	1973-01-04	1975-10-07	Janssen Pharmaceutica Nv	1-{55 1-{8 2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl{9 -4-piperidyl{56 -2-benzimidazolinones
US3929801A (en)	1973-11-20	1975-12-30	Janssen Pharmaceutica Nv	2-Benzimidazolinones
GR71865B (pt)	1978-03-20	1983-07-07	Ciba Geigy
DE2852945A1 (de)	1978-12-07	1980-06-26	Boehringer Sohn Ingelheim	Benzodioxanyl-hydroxyaethylpiperidyl- imidazolidinone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
US4329348A (en)	1979-02-26	1982-05-11	Ciba-Geigy Corporation	N-Oxacyclic-alkylpiperidines as psychostimulants
DE3124366A1 (de)	1981-06-20	1982-12-30	Hoechst Ag, 6000 Frankfurt	N-oxacyclyl-alkylpiperidin-derivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische praeparate und deren verwendung
FR2533584B1 (fr)	1982-09-28	1986-03-21	Pasteur Institut	Procede de detection du pouvoir mutagene de substances, susceptibles d'induire la deterioration d'adn cellulaires, mettant en jeu la production d'une reponse sos
DE3901814A1 (de)	1988-07-28	1990-02-01	Bayer Ag	Substituierte aminomethylzetraline sowie ihre heterocyclischen analoga
DE4140540A1 (de) *	1991-12-09	1993-06-17	Bayer Ag	Neue azaheterocyclylmethyl-chromane
SI9300097B (en) *	1992-02-27	2001-12-31	Janssen Pharmaceutica Nv	(benzodioxan, benzofuran or benzopyran) alkylamino) alkyl substituted guanidines
DE4319038A1 (de) *	1993-06-08	1994-12-15	Bayer Ag	Verwendung von teilweise bekannten substituierten Chromanen als Arzneimittel, neue Wirkstoffe und Verfahren zu ihrer Herstellung
RU2129556C1 (ru)	1993-08-19	1999-04-27	Жансен Фармасетика Н.В.	Производное дигидробензопирана, обладающее сосудосуживающим действием, промежуточные соединения, способы получения, фармацевтическая композиция и способ ее получения
US5541199A (en)	1995-06-02	1996-07-30	American Home Products Corporation	Chroman-2-ylmethylamino derivatives
FR2744451B1 (fr)	1996-02-01	1998-04-24	Pf Medicament	Nouvelles imidazolidinones, pyrimidinones, et 1,3-diazepin-2 -ones, leur preparation et leurs applications en therapeutique
US6133277A (en) *	1997-12-05	2000-10-17	Janssen Pharmaceutica N.V.	(Benzodioxan, benzofuran or benzopyran) derivatives having fundic relaxation properties
UA73123C2 (en)	1999-06-02	2005-06-15	Janssen Pharmaceutica Nv	Derivatives of benzodioxane, benzofuran or benzopyran substituted by pyrolidinyl, piperidinyl or homopiperidinyl
JO2352B1 (en)	2000-06-22	2006-12-12	جانسين فارماسيوتيكا ان. في	Compounds for the treatment of non-adaptation of the bottom of the uterus

2000
- 2000-05-23 DK DK00940267T patent/DK1187829T3/da active
- 2000-05-23 AU AU55256/00A patent/AU773773B2/en not_active Ceased
- 2000-05-23 DE DE60007124T patent/DE60007124T2/de not_active Expired - Lifetime
- 2000-05-23 JP JP2001502419A patent/JP2003501427A/ja not_active Withdrawn
- 2000-05-23 CA CA002374902A patent/CA2374902C/en not_active Expired - Lifetime
- 2000-05-23 EA EA200101236A patent/EA004645B1/ru not_active IP Right Cessation
- 2000-05-23 MX MXPA01012330A patent/MXPA01012330A/es unknown
- 2000-05-23 PL PL352112A patent/PL198552B1/pl not_active IP Right Cessation
- 2000-05-23 SK SK1703-2001A patent/SK285619B6/sk not_active IP Right Cessation
- 2000-05-23 PT PT00940267T patent/PT1187829E/pt unknown
- 2000-05-23 HU HU0201404A patent/HUP0201404A3/hu unknown
- 2000-05-23 IL IL14684000A patent/IL146840A0/xx active IP Right Grant
- 2000-05-23 HR HR20010868A patent/HRP20010868A2/hr not_active Application Discontinuation
- 2000-05-23 NZ NZ514993A patent/NZ514993A/en unknown
- 2000-05-23 BR BR0011237-2A patent/BR0011237A/pt not_active Application Discontinuation
- 2000-05-23 UA UA2001128825A patent/UA73122C2/uk unknown
- 2000-05-23 TR TR2001/03430T patent/TR200103430T2/xx unknown
- 2000-05-23 CZ CZ20014177A patent/CZ20014177A3/cs unknown
- 2000-05-23 SI SI200030293T patent/SI1187829T1/xx unknown
- 2000-05-23 EE EEP200100639A patent/EE04780B1/xx not_active IP Right Cessation
- 2000-05-23 ES ES00940267T patent/ES2212774T3/es not_active Expired - Lifetime
- 2000-05-23 US US09/980,452 patent/US6864273B1/en not_active Expired - Lifetime
- 2000-05-23 EP EP00940267A patent/EP1187829B1/en not_active Expired - Lifetime
- 2000-05-23 AT AT00940267T patent/ATE256125T1/de not_active IP Right Cessation
- 2000-05-23 CN CNB008083185A patent/CN1150191C/zh not_active Expired - Fee Related
- 2000-05-23 KR KR1020017013659A patent/KR100699512B1/ko not_active Expired - Fee Related
- 2000-05-23 WO PCT/EP2000/004746 patent/WO2000075136A1/en not_active Ceased
- 2000-05-24 TW TW089109971A patent/TWI289559B/zh not_active IP Right Cessation
- 2000-05-30 MY MYPI20002411A patent/MY120618A/en unknown
- 2000-06-01 AR ARP000102714A patent/AR033334A1/es unknown
2001
- 2001-11-28 BG BG106156A patent/BG65269B1/bg unknown
- 2001-11-29 IL IL146840A patent/IL146840A/en not_active IP Right Cessation
- 2001-11-29 ZA ZA200109860A patent/ZA200109860B/xx unknown
- 2001-12-03 NO NO20015903A patent/NO319953B1/no not_active IP Right Cessation
2004
- 2004-11-29 US US10/999,187 patent/US7273862B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
NO20015903L (no)	2001-12-03
TR200103430T2 (tr)	2002-06-21
US7273862B2 (en)	2007-09-25
IL146840A0 (en)	2002-07-25
EA200101236A1 (ru)	2002-08-29
ZA200109860B (en)	2003-05-28
CA2374902A1 (en)	2000-12-14
MXPA01012330A (es)	2002-07-30
PT1187829E (pt)	2004-04-30
ATE256125T1 (de)	2003-12-15
DK1187829T3 (da)	2004-04-13
CA2374902C (en)	2009-09-15
BG106156A (en)	2002-05-31
PL198552B1 (pl)	2008-06-30
PL352112A1 (en)	2003-07-28
SI1187829T1 (en)	2004-04-30
SK285619B6 (sk)	2007-05-03
HRP20010868A2 (en)	2003-04-30
ES2212774T3 (es)	2004-08-01
NZ514993A (en)	2003-05-30
IL146840A (en)	2006-12-10
NO319953B1 (no)	2005-10-03
US6864273B1 (en)	2005-03-08
HUP0201404A3 (en)	2005-02-28
AR033334A1 (es)	2003-12-17
BR0011237A (pt)	2002-03-05
TWI289559B (en)	2007-11-11
CZ20014177A3 (cs)	2002-05-15
EE04780B1 (et)	2007-02-15
DE60007124T2 (de)	2004-09-23
EA004645B1 (ru)	2004-06-24
CN1150191C (zh)	2004-05-19
US20050096378A1 (en)	2005-05-05
AU5525600A (en)	2000-12-28
HUP0201404A2 (en)	2002-08-28
AU773773B2 (en)	2004-06-03
EP1187829B1 (en)	2003-12-10
DE60007124D1 (de)	2004-01-22
JP2003501427A (ja)	2003-01-14
KR100699512B1 (ko)	2007-03-26
EE200100639A (et)	2003-02-17
WO2000075136A1 (en)	2000-12-14
CN1353707A (zh)	2002-06-12
EP1187829A1 (en)	2002-03-20
KR20010110806A (ko)	2001-12-13
NO20015903D0 (no)	2001-12-03
SK17032001A3 (sk)	2002-07-02
MY120618A (en)	2005-11-30
BG65269B1 (bg)	2007-11-30

Publication	Publication Date	Title
KR100500372B1 (ko)	2005-07-11	위장운동 조절성 3- 또는 4-치환된4-(아미노메틸)-피페리딘 유도체의 비사이클릭 벤즈아미드
DE69835372T2 (de)	2007-08-09	(benzodioxan, benzofuran, oder benzopyran) derivate mit fundic entspannungseigenschaften
UA73122C2 (en)	2005-06-15	Derivatives of benzodioxane, benzofuran or benzopyran substituted by aminoalkyl
UA74576C2 (en)	2006-01-16	Compounds of dioxinepyridines, a method for producing thereof (variants), a pharmaceutical composition based thereon and a method for producing thereof
UA73123C2 (en)	2005-06-15	Derivatives of benzodioxane, benzofuran or benzopyran substituted by pyrolidinyl, piperidinyl or homopiperidinyl
JP5437814B2 (ja)	2014-03-12	２−ピペラジン−１−イル−３Ｈ−イミダゾ［４，５−ｂ］ピリジン誘導体
MXPA00005524A (en)	2002-05-09	(benzodioxan, benzofuran or benzopyran) derivatives having fundic relaxation properties